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Volumn 74, Issue 1, 2009, Pages 212-221

Synthesis of 2-substituted indoles and indolines via Suzuki-Miyaura coupling/5-endo-trig cyclization strategies

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL EQUATIONS; CHEMOSELECTIVE; CROSS COUPLINGS; EFFICIENT SYNTHESES; NEW STRATEGIES; ONE POTS; RADICAL CYCLIZATIONS; SUBSTITUTED INDOLES; SYNTHESIS OF;

EID: 58149314193     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo801985a     Document Type: Article
Times cited : (44)

References (144)
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    • Additions and Corrections
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    • For a preliminary report of this work, see ref 11d
    • For a preliminary report of this work, see ref 11d.
  • 49
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    • Recently, a very similar synthesis of N-aryl enecarbamates has appeared: Cottineau, B.; Gillaizeau, I.; Farard, J.; Auclair, M.-L.; Coudert, G. Synlett 2007, 1925.
    • Recently, a very similar synthesis of N-aryl enecarbamates has appeared: Cottineau, B.; Gillaizeau, I.; Farard, J.; Auclair, M.-L.; Coudert, G. Synlett 2007, 1925.
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    • The choice of the protective group was found to be crucial for the success in the preparation of enol phosphates. Upon treatment of N-(o-bromophenyl)acetanilides having other types of electron-withdrawing, N-protective groups, such as p-toluenesulfonyl, benzoyl, or trifluoroacetyl, with KHMDS in the presence of (PhO)2P(O)Cl only resulted in loss of the acetyl group
    • 2P(O)Cl only resulted in loss of the acetyl group.
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    • Reports on leaving-group selectivities of palladium(0)-catalyzed reactions: (a) Echavarren, A. M.; Stille, J. K. J. Am. Chem. Soc. 1987, 109, 5478.
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    • We have found that the use of 10 mol, of Pd(OAc)2/Cy 3P catalyst (Pd/L, 1/2) in the presence of Cs2CO 3 (3 equiv) in 1,4-dioxane at 100°C also gave indole 8 in 89% yield. In contrast, the use of Pd2dba3/Davephos, Pd2dba3/ S-Phos, Pd2dba3/Cy 3P·HBF4, or Pd2dba3/t- Bu3P·HBF4 catalyst was less effective for the present reaction
    • 4 catalyst was less effective for the present reaction.
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    • For recent examples of 5-endo Heck cyclizations excluding enamine-type compounds, see: (a) Sakoda, K.; Mihara, J.; Ichikawa, J. Chem. Commun. 2005, 4684.
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.